Water → 2-[(4-Bromo-2-fluoro-phenyl)methyl]-6-phenyl-thiazinane 1,1-dioxide

HRID 517296Notes

Reaction equation

HRID 517296 reaction equation
[C:1]1([CH:7]2[S:12](=[O:14])(=[O:13])[NH:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[C:18]([F:24])[CH:17]=1.[H-].[Na+].O>CN(C)C(=O)C.CCOC(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:11]2[CH2:10][CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:12]2(=[O:14])=[O:13])=[C:18]([F:24])[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 713039976-Phenyl-1,2-thiazinane 1,1-dioxide

Product 1

HCID 867092782-[(4-Bromo-2-fluoro-phenyl)methyl]-6-phenyl-thiazinane 1,1-dioxideYield 70%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-phenyl-1,2-thiazinane 1,1-dioxide (300 mg, 1.42 mmol) and 4-bromo-1-(bromomethyl)-2-fluorobenzene (456 mg, 1.7 mmol) in N,N-dimethylacetamide (5 mL) at 0° C. was added sodium hydride (60% in mineral oil) (68 mg, 1.85 mmol) and the reaction was stirred at room temperature for 2 hours. Water was added and the reaction was diluted with EtOAc, washed with brine, dried with MgSO4, filtered and purified by silica gel column chromatography (0-60% EtOAc/heptane) to give 2-(4-bromo-2-fluorobenzyl)-6-phenyl-1,2-thiazinane 1,1-dioxide (396 mg, 70% yield). LCMS (ESI), m/z, 398 [M+H]+.

Workup

  1. washwashed with brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. custompurified by silica gel column chromatography (0-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-1b0c4bd394684faa98feed50371c2f01
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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